Reaktion #155334

Reaktionsgleichung

Hydrazine hydrate

2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dione

→

1-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Ausbeute 94.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 4 hours
3. 3
   EinengenThe resulting mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONa 5N aqueous sodium hydroxide solution was added to the thus-obtained residue
5. 5
   Extraktionthe resulting mixture was subjected to extraction
6. 6
   WaschenThe thus-obtained organic layer was sequentially washed with water
7. 7
   Trocknenan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure

Vorschrift

Hydrazine hydrate (0.62 ml, 12.8 mmol) was added to an ethanol solution (60 ml) of 2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dione (2.0 g, 3.88 mmol) and heated under reflux for 4 hours. The resulting mixture was concentrated under reduced pressure, a 5N aqueous sodium hydroxide solution was added to the thus-obtained residue, and then the resulting mixture was subjected to extraction using dichloromethane. The thus-obtained organic layer was sequentially washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, giving a yellow oily 1-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (1.4 g, yield: 94%).

Quelle